Cited by 118Free Radicals and AntioxidantsRedox biology and oxidative stressAntioxidant Activity and Oxidative Stress

Radical–radical reactions of superoxide: A potential route to toxicity

Winterbourn, Christine C., Kettle, Anthony J.·2003·Biochemical and Biophysical Research Communications

Abstract

Superoxide reacts with many radicals, such as phenoxyl radicals, at near diffusion-controlled rates. These reactions are usually considered to be repair processes and have received little biological attention. However, addition of superoxide to give hydroperoxides and secondary oxidation products can also occur. The relative contributions of addition and repair vary depending on the properties of the phenol. With tyrosine, addition to give tyrosine hydroperoxide predominates, but in peptides the efficiency of hydroperoxide formation depends on the proximity of free amine groups. Radicals from other phenolic compounds, such as alpha-tocopherol and serotonin, also undergo addition reactions with superoxide. Physiologically, these reactions are likely to be more significant than dimerization when both radicals are generated together. They warrant attention as potential contributors to superoxide toxicity.

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Crossref · 10.1016/s0006-291x(03)00810-6

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76 of 76 references verified0 citation errors · 0 not checkable

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  • The tyrosine hydroperoxide can be formed in the ortho or para position relative to the phenoxyl radical due to resonant forms of Tyr.

    “The hydroperoxide, due to the resonant forms of Tyr, can be formed in the ortho or para position with respect to the phenoxyl radical [138,139,140], Figure 51 and Figure 52.”

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Authors
Winterbourn, C. C., & Kettle, A. J.
Corresponding author
Winterbourn, Christine C.
Venue
Biochemical and Biophysical Research Communications
Publisher
Elsevier BV
Published
2003-06
Volume
305
Issue
3
Pages
729-736
ISSN
0006-291X (ISSN-L)
OpenAlex
W1967305386
Cited by
118
References
76
Citations by year
2026: 3 · 2025: 2 · 2024: 2 · 2023: 6 · 2022: 2 · 2021: 7 · 2020: 3 · 2019: 3 · 2018: 2 · 2017: 4 · 2016: 3 · 2015: 6 · 2014: 10 · 2013: 4 · 2012: 8
FWCI
4.92
Type
journal article
Language
en
Open access
closed
Locations
  • Biochemical and Biophysical Research Communications (publishedVersion)
  • PubMed (publishedVersion)
Funders
Health Research Council of New Zealand
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
  • Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
Keywords
superoxide, phenoxyl radicals, radical-radical reactions, hydroperoxide formation, phenol oxidation, alpha-tocopherol, serotonin, radical dimerization, diffusion-controlled reaction
MeSH terms
Animals, Free Radicals, Indoles, Models, Chemical, Nitric Oxide, Peptides, Peroxides, Phenols, Proteins, Superoxides, Tyrosine, Vitamin E

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